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  1. The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch
  2. 20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough
20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch · Aug 8, 2026

David Frankel on the AI boom's roadkill, why founders should avoid multi-stage seed money, and why 'triple, triple, double, double' is still a winning formula.

Never Turn Down an Exceptional Founder Over a Small Ownership Percentage

Obsessing over hitting a specific ownership target is a critical error for seed investors, leading them to miss generational companies. For truly exceptional founders, the right approach is to take whatever allocation is available, even if it's only 1-2%, rather than passing on the opportunity entirely. The access to greatness is what matters.

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough thumbnail

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 days ago

Venture Pro-Rata Rights Are an 'Original Sin' That Harms Entrepreneurs

Pro-rata rights, often seen as a crucial term for VCs, are fundamentally misaligned with founder interests. They function as a call option against the entrepreneur, creating negative signaling and complications in future funding rounds. Investors should have to re-earn their right to invest more money in every subsequent round.

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough thumbnail

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 days ago

Startup 'Nepo Babies' with Deep Vertical Expertise Have an Unfair Advantage

The most successful founders are often 'nepo babies,' not of wealth, but of industry. Individuals who grew up in a specific vertical—like T.J. Parker in his dad's pharmacy (PillPack)—possess an unparalleled edge. This deep, almost innate understanding of a market's problems is a powerful predictor of success that investors should actively seek.

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough thumbnail

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 days ago

A Billion-Dollar Valuation is The New Series A

The benchmark for a successful venture outcome has shifted dramatically. Where investors once aimed for a 20x return on a $50 million post-money valuation to reach a billion-dollar outcome, they now underwrite deals at a $1 billion entry valuation with the expectation of a $20 billion+ exit, reflecting massive outcome expansion.

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough thumbnail

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 days ago

Mega-Fund Seed Checks Orphan 95% of Startups When Junior Partners Leave

The majority of entrepreneurs who take seed money from large, multi-stage funds are ultimately harmed. The junior investor who championed them often moves on, leaving the company "orphaned" within the firm. Without an internal champion, they lose the mandate for crucial follow-on funding when they inevitably miss aggressive growth targets.

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough thumbnail

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 days ago

Applied AI Was the Winning Theme a Decade Ago; Today's Winners Are Already Funded

Momentum investing chases current themes like AI, but the biggest returns come from investing 5-10 years before they become hype cycles. Founder Collective's Fund II winners (Shield AI, Verkada) were all 'Applied AI' companies funded around 2016, long before it was a popular thesis. The job is to find the next non-obvious theme now.

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough thumbnail

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 days ago

The Startup World Has Many 'Founders' but Few 'Entrepreneurs'

Becoming a 'founder' has been normalized, but this masks a shortage of true 'entrepreneurs.' An entrepreneur possesses a different level of fortitude and a unique ability to navigate the steep learning curves required of a CEO—particularly in recruiting and management—which many founders fail to develop when the tide goes out.

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough thumbnail

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 days ago

Boutique Seed Funds Act as an Insurance Policy for Founders Taking Multi-Stage Money

Founders backed by large, multi-stage funds are increasingly bringing in smaller, specialized seed funds. They see these boutique VCs as an "insurance policy"—a more patient, aligned partner who will stick by them if the larger, less-focused fund abandons them for not hitting aggressive growth targets.

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough thumbnail

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 days ago

"Triple, Triple, Double, Double" Growth Is Still a Viable Venture Path

Contrary to the modern venture mantra of hyper-growth or bust, the classic "T2D3" model is not dead. Patient investors recognize that great companies take over a decade to build. Seed extension rounds for companies abandoned by momentum investors can present the most opportune moments to invest, as reality often takes longer than the hype cycle allows.

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough thumbnail

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 days ago

Market Leaders Are Now Being Cannibalized Before They Can Reach Liquidity

The speed of technological innovation, particularly with AI, has accelerated dramatically. This creates a new risk where established private market leaders can be disrupted and 'cannibalized' by a new wave of technology before they have had the chance to achieve a major liquidity event like an IPO or acquisition.

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough thumbnail

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 days ago

Founder Collective Stays Small by Making Its GPs the Largest LPs

To maintain discipline and resist raising larger funds, Founder Collective ensures its General Partners are collectively the largest Limited Partner. This structure forces intense alignment with other LPs, prioritizing cash-on-cash returns (DPI) over the asset-gathering and management fees that larger funds often optimize for.

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough thumbnail

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 days ago

$50-100M Seed Funds Are Too Big to Be Collaborative but Too Small to Lead

Seed funds in the $50-$100M range are stuck in a 'danger zone.' They are too large to write small, friendly checks ($100-250k) and be truly collaborative party-round participants. However, they are too small to lead the increasingly common $8-10M seed rounds, making it difficult to deploy capital effectively and compete.

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough thumbnail

20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough

The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch·4 days ago